4,4-Dimethylpent-2-yn-1-ol → 4,4-Dimethyl-1-pentanol

To a stirred solution of 4,4-dimethyl-pent-2-yn-1-ol (3.1 g, 27.6 mmol) in ethanol (30 ml) is added 10% palladium on carbon (0.3 g). The mixture is stirred under an atmosphere of hydrogen for 16 h. The reaction mixture is filtered through a pad of celite and the celite bed is washed with methanol (10 ml). The filtrate thus obtained is concentrated and the crude product is purified by column chromatography (5-10% ethyl acetate/hexane) to afford 4,4-dimethyl-pentan-1-ol and 4,4-dimethyl-pentan-1-al. To a stirred solution of 4,4-dimethyl-pentan-1-al (0.85 g, 7.45 mmol) in methanol (12 ml) is added sodium borohydride (0.56 g, 14.9 mmol) at 0° C. The reaction mixture is stirred at RT for 1.5 h. On completion, the solvent is evaporated and then diluted with ethyl acetate (30 ml). The organic layer is washed with water (2×20 ml), brine (20 ml), dried over sodium sulfate and concentrated affording 4,4-dimethyl-pentan-1-ol (1.52 g, 13.1 mmol, 48%).

1. filtrationThe reaction mixture is filtered through a pad of celite
2. washthe celite bed is washed with methanol (10 ml)
3. customThe filtrate thus obtained
4. concentrationis concentrated
5. customthe crude product is purified by column chromatography (5-10% ethyl acetate/hexane)

ORD record

ord-36e5fc7b903e454aa4afd404b2ce3c98

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108936B2